Electroinitiated polymerization of compositions having a 1,1-disubstituted alkene compound

• US 9,217,098 B1
• Filed: 06/01/2015
• Issued: 12/22/2015
• Est. Priority Date: 06/01/2015
• Status: Active Grant

• Current Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Original Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Inventors: Sullivan, Jeffrey M., Stevenson, Peter Rulon
• Primary Examiner(s): CHEUNG, WILLIAM K
• Application Number:
  US14/727,285
• Time in Patent Office: 204 Days
• Field of Search: 526/236, 526/319, 525/10
• US Class Current: 1/1
• CPC Class Codes: C08F 2/58 Polymerisation initiated by direct application of electric current electrolytic processes, e.g. electrophoresis C25
• CPC Class Codes: C08F 20/16 of phenols or of alcohols containing two or more carbon atoms
• CPC Class Codes: C08K 3/36 Silica
• CPC Class Codes: C08L 2201/10 Transparent films; Clear coatings; Transparent materials
• CPC Class Codes: C08L 35/02 Homopolymers or copolymers of esters C08L35/06, C08L35/08 take precedence
• CPC Class Codes: C09J 4/00 Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
• CPC Class Codes: C25B 3/29 Coupling reactions

Abstract

A method of initiating polymerization of a composition formed of a 1,1-disubstituted alkene compound includes contacting the composition with a substrate and passing an electrical charge through the composition. The composition can also be electrografted to the substrate or include conductive synergists.

Claims

1. A method of initiating polymerization comprising:

contacting a polymerizable composition with a substrate, the polymerizable composition comprising one or more 1,1-disubstituted alkene compounds; and

passing an electrical charge through the polymerizable composition to initiate polymerization; and

wherein the polymerizable composition undergoes living anionic polymerization after polymerization is initiated.

2. The method of claim 1, wherein the one or more 1,1-disubstituted alkene compounds are selected from the group consisting of methylene malonates, methylene β

-ketoesters, methylene β

-diketones, dialkyl disubstituted vinyls, dihaloalkyl disubstituted vinyls, monofunctional, difunctional or multifunctional monomers, oligomers, or polymers thereof, and combinations thereof.

3. The method of claim 2, wherein the one or more 1,1-disubstituted alkene compounds comprise one or more of diethyl methylene malonate, fenchyl methyl methylene malonate, methylmethoxy ethyl methylene malonate, hexyl methyl methylene malonate, and dibutyl methylene malonate.

4. The method of claim 1, wherein the polymerizable composition is substantially free of a solvent.

7. The method of claim 1, wherein the electrical charge is provided by one or more of an electrochemical charge, direct current, alternating current, and an electron beam.

8. The method of claim 7, wherein the electrical charge comprises about 30 volts or more and about 1 amp or more.

9. The method of claim 1, wherein the polymerizable composition is an adhesive, and the polymerizable composition has a tensile shear strength of about 800 psi to about 2,500 psi when cured.

10. The method of claim 1, wherein the polymerizable composition electrografts to the conductive substrate.

11. The method of claim 1, wherein the polymerizable composition has an impact resistance of about 6 J/in² to about 7 J/in².

12. The method of claim 1, further comprising the step of quenching polymerization before curing of the polymerization composition has been reached by adding a weak acid.

13. The method of claim 1, wherein the conductive substrate comprises one or more of aluminum, steel, stainless steel, copper, brass, metal alloy, conductive polymer, polymer composites containing conductive materials, or graphite.

14. The method of claim 1, wherein the polymerizable composition is disposed between the conductive substrate and a second conductive substrate;

and

wherein the electrical charge is passed through the first conductive substrate to the second conductive substrate.

5. A method of initiating polymerization comprising:

contacting a polymerizable composition with a substrate, the polymerizable composition comprising one or more 1,1-disubstituted alkene compounds and one or more conductive synergists selected from the group of non-nucleophilic conductive materials; and

passing an electrical charge through the polymerizable composition to initiate polymerization; and

wherein the one or more conductive synergists reduce the set time of the polymerizable composition to about 20 minutes or less once polymerization is initiated.

15. The method of claim 5, wherein the polymerizable composition is substantially free of a solvent.

16. The method of claim 5, wherein the polymerizable composition electrografts to the conductive substrate.

17. The method of claim 5, wherein the conductive substrate comprises one or more of aluminum, steel, stainless steel, copper, brass, metal alloy, conductive polymer, polymer composites containing conductive materials, or graphite.

6. A method of initiating polymerization comprising:

contacting a polymerizable composition with a substrate, the polymerizable composition comprising one or more 1,1-disubstituted alkene compounds and one or more acid stabilizers and one or more free radical stabilizers, and wherein the one or more acid stabilizers and the one or more free radical stabilizers are included in a ratio of about 10;

100 to a ratio of 10;

1,000 or more; and

passing an electrical charge through the polymerizable composition to initiate polymerization.

18. The method of claim 6, wherein the polymerizable composition is substantially free of a solvent.

19. The method of claim 6, wherein the polymerizable composition electrografts to the conductive substrate.

20. The method of claim 6, wherein the conductive substrate comprises one or more of aluminum, steel, stainless steel, copper, brass, metal alloy, conductive polymer, polymer composites containing conductive materials, or graphite.